Synthesis, in vitro evaluation and molecular docking studies of thiazole derivatives as new inhibitors of α-glucosidase

Rahim, Fazal; Ullah, Hayat; Javid, Muhammad Tariq; Wadood, Abdul; Taha, Muhammad; Ashraf, Muhammad; Shaukat, Ayesha; Junaid, Muhammad; Hussain, Shafqat; Rehman, Wajid; Mehmood, Rashad; Sajid, Muhammad; Khan, Muhammad Naseem; Khan, Khalid Mohammed

doi:10.1016/j.bioorg.2015.06.006

Cited by 119 publications

(33 citation statements)

References 32 publications

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“…The structure of α‐amylase was obtained from PDB (ID: 1OSE). However, the structural information of α‐glucosidase from Saccharomyces cerevisiae is not available yet . Therefore, it is necessary to conduct homologous modeling on the basis of isomaltose from S. cerevisiae .…”

Section: Methodsmentioning

confidence: 99%

Inhibition of glycosidase by ursolic acid: in vitro, in vivo and in silico study

et al. 2019

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BACKGROUND: Controlling the blood glucose level is an effective method to reduce type 2 diabetes and prevent diabetes-related complications. Ursolic acid is a plant extract that can reduce postprandial hyperglycemia effectively. This study aimed to explore the inhibitory effect and interaction mechanism of ursolic acid against -amylase and -glucosidase. RESULTS: In this study, the effect of ursolic acid on glycosidase was studied in vitro, in vivo, and in silico. The half-maximal inhibitory concentration (IC 50 ) of ursolic acid on -amylase and -glucosidase was 0.482 ± 0.12 mg mL −1 and 0.213 ± 0.042 mg mL −1 , respectively. The results of enzymatic kinetics showed that ursolic acid inhibited -amylase and -glucosidase activity in a non-competitive manner. The fluorescence spectrum showed that the combination of ursolic acid and glycosidase caused the intrinsic fluorescence quenching of glycosidase. The observation of starch granules revealed that the activity of -amylase was inhibited and the hydrolysis of starch granules was prevented in the presence of ursolic acid. Molecular docking results showed that ursolic acid bound to the inactive site of -amylase and -glucosidase through the formation of ursolic acid-glucosidase complex. Ursolic acid interacted with -amylase and -glucosidase mainly through hydrogen bonding. The postprandial hypoglycemic effect of ursolic acid in C57BL/6J mice showed that the high concentration of ursolic acid could quickly reduce postprandial blood glucose level.CONCLUSION: Ursolic acid can be considered as a natural ingredient in functional foods to control postprandial blood glucose levels and prevent diabetes by delaying the digestion of starch in foods.

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Section: Methodsmentioning

confidence: 99%

Inhibition of glycosidase by ursolic acid: in vitro, in vivo and in silico study

et al. 2019

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“…Thiazole are important class of heterocyclic compounds found in many potent biologically active molecules such as thiobendazol (anthelmintic drug) [20], riluzolr (anticonvulsant drug) [21] and talipexzol (antiparkinsonian drug) [22]. Its application also found in drug development for the treatment of inflammation [23]. Recently thiazole analogs have been also reported as antiglycating agent, anti-diabetic and as a potent inhibitor for cholinesterase [24][25][26].…”

Section: Bche I N H I B I T T H E a C T I V I T Y O F T H E E N Z Ymentioning

confidence: 99%

“…The obtained products (1mmol) were then reacted and refluxed with (1mmol) of methoxy or chloro substituted phenacyl bromide for 3-5 hours. After reaction completion the mixture was filter and wash with hexane to yield pure products [23,28,29]. Different spectroscopic techniques, such as EI-MS, 1 H NMR and 13 C NMR were used to determine the structure of all analogs.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, molecular docking, acetylcholinesterase and butyrylcholinesterase inhibitory potential of thiazole analogs as new inhibitors for Alzheimer disease

Rahim

Javed

Ullah

et al. 2015

Bioorganic Chemistry

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127

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“…On the other hand, thiazole derivatives are considered as another important class of heterocyclic compounds, which displayed a wide range of pharmacological activities such as anti-inflammatory [ 20 ], anticancer [ 21 ], anticonvulsant [ 22 ], and antibacterial [ 23 ]. It is interesting that numerous studies pointed out thiazole could be used as a useful moiety in the design of potent α-glucosidase inhibitors [ 24 , 25 , 26 , 27 , 28 ]. For example, compound series V [ 25 ], VI [ 28 ], and VII [ 26 ] displayed potent α-glucosidase inhibitory activity ( Figure 1 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Biological Evaluation, and Molecular Docking Studies of Novel Isatin-Thiazole Derivatives as α-Glucosidase Inhibitors

Xie

Wang

et al. 2017

Molecules

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A series of novel isatin-thiazole derivatives were synthesized and screened for their in vitro α-glucosidase inhibitory activity. These compounds displayed a varying degree of α-glucosidase inhibitory activity with IC50 ranging from 5.36 ± 0.13 to 35.76 ± 0.31 μm as compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 μm). Among the series, compound 6p bearing a hydroxyl group at the 4-position of the right phenyl and 2-fluorobenzyl substituent at the N1-positions of the 5-methylisatin displayed the highest inhibitory activity with an IC50 value of 5.36 ± 0.13 μm. Molecular docking studies revealed the existence of hydrophobic interaction, CH-π interaction, arene-anion interaction, arene-cation interaction, and hydrogen bond between these compounds and α-glucosidase enzyme.

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Synthesis, in vitro evaluation and molecular docking studies of thiazole derivatives as new inhibitors of α-glucosidase

Cited by 119 publications

References 32 publications

Inhibition of glycosidase by ursolic acid: in vitro, in vivo and in silico study

Inhibition of glycosidase by ursolic acid: in vitro, in vivo and in silico study

Synthesis, molecular docking, acetylcholinesterase and butyrylcholinesterase inhibitory potential of thiazole analogs as new inhibitors for Alzheimer disease

Synthesis, Biological Evaluation, and Molecular Docking Studies of Novel Isatin-Thiazole Derivatives as α-Glucosidase Inhibitors

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